The Closing: 20th Anniversary Edition

In hindsight, asking Sam Zell when he planned to ride off into the sunset (on one of his Ducati motorbikes, perhaps) may have been misguided. Real estate titans don’t retire; they typically get carried out in a body bag. It’s the one commonality across nearly 200 interviews with the biggest names in the business. If you’re thinking of packing it in, if you’re not having fun at the highest level, you’re probably a ways from the highest level.

“The Closing” pages at the end of each issue have been home to The Real Deal’s signature interview since 2006, three years into the life of this magazine. Readers have turned to it for inspiration, war stories and to live vicariously through the developers, financiers, architects, politicians, economists and dealmakers who’ve shaped America’s biggest cities.

In this special 20th anniversary edition, we’re looking back at some of the most memorable exchanges with the most memorable characters in the business: high-powered female executives on dominating a male-dominated industry, grizzled moguls on their biggest regrets, outsiders who battled prejudice on their way to becoming the ultimate insiders, titans on juggling their 24/7 careers with marriage and parenthood and bigwigs enjoying the (ample) fruits of their labor.

At their best, the interviews are often hilarious, sometimes philosophical, occasionally provocative, but always revealing: They transcend the news of the moment and get to the core of the person behind the headline-grabbing deals.

These exchanges have been edited for length and clarity. Interviews were carried out beginning in 2006, so company affiliations and circumstances may have changed — in some cases dramatically.

Rich people stuff

Gambling on real estate comes with outsized risks — the path from prince to pauper is a well-traveled one — but also serious rewards. Below are some of the most colorful examples of moguls living the good life.

Gil Dezer
Dezer International (2021)

You live the “fuck-you money” lifestyle you sell. Do you have any regrets about being so out there?
I don’t necessarily show it off.

You’ve got that car collection. You’re wearing that giant gold watch.
I never really thought about it that way. I have an anonymous Instagram account where all I do is show my toys. I have 70,000-odd followers. Some people tell me, “Hey, you’re my inspiration.” Which makes me feel bad. I hope they find better inspiration.

I have a Bugatti Veyron. They made only 300 of them. I have a Porsche 918; they made only 918 of them. I have number 305, which is cool for Miami [area code 305]. These things are assets like any other asset. But you get to play with them. You can’t play with your Coca-Cola stock.

Jed Walentas
Two Trees Management (2017)

Do you make as much money as you’d like?
The money is a tremendous privilege. It lets me do whatever the fuck I want whenever I want, which is an amazing way to go through life.

Edward Minskoff
Edward J. Minskoff Equities (2008)

What does your art collection consist of?
It’s 100 percent 20th-century Contemporary. It ranges from the old guard, which is Picasso — we have huge numbers of his works in our collection — paintings, drawings, sculpture. Jackson Pollock, Roy Lichtenstein, [Willem] de Kooning … right up to the new guard. We have quite a few of Richard Prince, Damien Hirst, [Jean Michel] Basquiat and Jeff Koons.

Aby Rosen
RFR Realty (2007)

How much money do you have in your wallet right now?
Probably a couple thousand bucks. This is not a cash society anymore, but I always have a couple of thousand bucks in my pocket.

What’s the most expensive piece of art you own?
Francis Bacon; it’s probably $15 million.

Aren’t you afraid of getting mugged?
No. Nobody mugs anybody in New York City anymore. This is the safest city, I swear to God.

Richard Mack
Mack Real Estate Group (2014)

Do you get much time with your three boys?
Yes. We ski a lot in the winter. I’m taking them to Chamonix [in France] to do some off-piste in March.

Leslie Himmel
Himmel + Meringoff (2013)

Do you make as much money as you’d like to make?
Every time I’ve reached the next bar, it seems like that bar is too low.

Todd Michael Glaser
Developer (2022)

How much cash do you have in your wallet?
A lot. I’m a cash guy. Usually I have $4,000 or $5,000. ’Cause I’m the type of guy that if a job site’s behind and it’s late at night and everybody’s packing up, I’ll throw $500 to each group. The next thing you know, they’re working.

Michael Stern
JDS Development (2016)

What’s the last thing you purchased?
Do buildings count?

Richard LeFrak
LeFrak Organization (2016)

Forbes estimates you’re worth $6.6 billion.
I always ask, if I don’t know how much money I have and I don’t care, why should they?

Stephen Ross
Related Companies (2014)

Where do you live now?
In the Time Warner Center, which I built.

You work there, too. Are there days you feel like you never leave the building?
When the weather’s bad, I’ve gone for two or three days without going outside. I eat at the restaurants and go to Dizzy’s [the nightclub at Jazz at Lincoln Center].

Barbara Fox
Fox Residential (2012)

What’s your greatest fear?
If something happened to my husband and me, I really worry I wouldn’t be able to keep my animals together. I made a provision for that in my will, that they have to stay together.

Louise Sunshine
The Sunshine Group (2007)

How about any shows for entertainment?
“Desperate Housewives.”

What do you like about the show?
I was once one of them. … Been there, done that.

David Bistricer
Clipper Equity (2016)

Do you have any vices? My vice is money. I like to make money.

The extreme sport of dealmaking

Those who only do what’s in the real estate manuals only make it so far. This remains a game for cowboys, and many of them have shared their most interesting experiences.

Dov Hertz
DH Property Holdings (2021)

What are your most effective negotiating tactics?
I went into business with a guy named Armand Lasky, and in ’89 we borrowed money from a Japanese bank for a building in Philadelphia. It was a turnaround situation, and we realized our tenant was not covered by a [subordination and nondisturbance agreement]. So if a lender takes back the building, he can wipe out the lease. We knew that our angle to buy out this tenant was to let him know that he had vulnerability in his lease.

Then the market crashed and we couldn’t sustain the building but [the tenant] didn’t believe me, because who buys a building and six months later is giving it back to the bank? So I hired two Japanese actors to walk around and make a lot of noise in Japanese. The guy calls me the next day and says, “What the hell is going on?” I said, “Well, they flew down from Japan and wanted to see what it is that they’re going to be taking back.” And he was willing to negotiate after that.

John Catsimatidis
Red Apple Group (2011)

What’s the story with your pilot being held hostage?
We were in the airplane and jet leasing business. It was 1996. We were stuck with a bunch of 727s. The only place to sell them was Africa. We delivered the last plane [to West African mogul Foutanga Babani Sissoko], but they took away our pilot’s passport in an attempt to reopen negotiations on the price. He wasn’t really a hostage. He was in a luxury hotel with many women and lots of food.

So what’d you do?
Lowered the price.

Julien Studley
Studley (2008)

Were you in the army?
I was drafted in 1950 when I was 23. My assignment was to be in the 278th Regimental Combat Team [of the Tennessee National Guard]. They filled this southern reserve unit with people from the Northeast. I was hardly from the Northeast. I wasn’t a citizen. My English was abominable. I had never gone to school. I was supposed to go to the front of the line and zero in on enemy short-term artillery. You had to climb up a tree, put up speakers, and if they shot, you could triangulate where they were located. It’s a long story, but I went to the Pentagon and got transferred into psychological warfare.

David Rozenholc
David Rozenholc & Associates (2018)

How long do your cases take?
I’ve represented tenants for 30 years where I still haven’t settled. I have a case from 1984. If my clients do not end up in a better position, I won’t settle. And if you fuck with me, I’ll fuck you for sport.

For sport?
You’ll pay extra because you fucked with me and my clients.

Ben Brafman
Brafman & Associates (2018)

In your early years, you represented a few alleged mobsters. Were you ever worried about your own safety?
If you wanted to become a trial lawyer, the only people going to trial were people who the government alleged to be members of organized crime. And the greatest criminal defense lawyers of my generation were the people trying those cases. Working my way into that league was great. It was flattering. I was personally never worried or afraid because with respect to certain clients, I was able to keep my distance.

Robert Verrone
Iron Hound Management (2016)

You once sent funeral roses to Joseph Chetrit when he went to another lender on a deal. Do you still do things like that?
We were pitching a workout the other day with special servicer LNR. As a joke, we mailed LNR a Barbie doll with a bunch of toy dinosaurs around it because its collateral was surrounded by a bunch of buildings our sponsor owned in New Jersey. My team bought the toys and stapled them onto cardboard.

Carrie Chiang
Corcoran Group (2019)

How do you vet clients?
There are so many fake buyers. My God, I could write a book. I can smell when fake people come up. One of the most interesting situations was when I was selling four apartments at Trump International Tower. There was a guy who claimed he was the son of Sara Lee Schupf [of dessert brand fame]. He came with a pregnant wife and said they lived in Connecticut. He said he wanted to buy the whole package. It just sounded a little bit ridiculous. During the showing, something felt wrong. It turned out he was a con artist. The Chicago police were trying to find him.

Sharif El-Gamal
Soho Properties (2010)

What is your response when people demand that you move your interfaith center project [away] from Ground Zero?
But why? Why should I have to? I’m an American. It’s my right. This isn’t about sensitivities or anything. I don’t hold my faith accountable for what happened [on 9/11] and I don’t hold myself accountable for what happened.

Roy March
Eastdil Secured (2017)

You worked with Harry Macklowe on the deal of the century, his acquisition of the GM Building. What was your impression of him?

All I remember was this very eccentric person who had latched onto the fact that I was at Eastdil and involved in the GM Building. We went on a sailboat, and I saw he was sketching my wife’s foot — her foot bracelet. If that isn’t a little eccentric…

Casualties of war

Any glittering real estate career is filled with failures. There’s no such thing as a perfect track record. Here, moguls reflect on their biggest stumbles.

Sam Zell
Equity Group (2017)

What’s the worst deal you’ve ever done?
I lost the most amount of money on the Tribune. But let me put it this way — my goal is to be right seven out of 10 times. … I’m not going to get all hits, but what I’ve got to do, and what a lot of other people in my field have not done well, is assess the scale of the risk. I start by saying, “Can I afford to lose it all?”

Donald Trump
Trump Organization (2010)

When you look back at your career, what would you do differently?
You have to learn from your successes and your failures. And if you don’t learn from mistakes, then you’re a fool. Now, ideally you want to watch other people and learn from their mistakes, because that’s less costly and less traumatic.

Which of your decisions have gone the other way?
Many of the decisions don’t go well because of timing. You’ll buy a building, make a great deal on a building, and then the market crashes. All of a sudden your great deal isn’t so good. In the early ’90s, they changed the tax code. You bought stuff and they changed the rules of the game. It’s hard to blame yourself for that.

Ziel Feldman
HFZ Capital Group (2013)

What’s been your biggest career mistake?
I was involved in investing in a rock-and-roll amusement park in Myrtle Beach. Our timing was a little off. We finished it under budget and early, but it opened in the summer of 2008, which was the worst time to open up. Most people drive to Myrtle Beach, and gas prices were at a record high. It was very hard to attract people. It went bankrupt and was sold.

David Lichtenstein
Lightstone Group (2016)

Was the Extended Stay bankruptcy your lowest career moment?
There have been many hair-raising moments. … I have a whole book entitled “Stupid Stuff I Have Done.” It’s very thick.

Chris Schlank
Savanna (2014)

What are your bad habits?
I’ve got a bad temper and I tend to talk too much. My worst habit is saying things how I see them out loud. I’m trying to develop a filter.

Yair Levy
Time Century Holdings (2014)

There were reports of you pummeling Kent Swig with an ice bucket over the dispute at the Sheffield.
We had a meeting, and he started screaming and fighting with my lawyer. He stood up, and I said, “Sit down.” He came at me and I grabbed the ice bucket to protect myself. He’s a much younger man. He got wet and I dropped the bucket. He tried to use it for publicity and make me out to be the bad guy.

Ralph Herzka
Meridian Capital Group (2017)

I heard that you once got shot by a stranger while you were out on business. What happened?
We’re not going to talk about that.

Denting the glass ceiling

Real estate is a boys club, and the private nature of it means that much-needed change has come far more slowly than in other major industries. The women who’ve made it to the very top have all the requisite traits needed to be there — ferocity, talent, a cartoonish level of drive — and then some. Over the years, TRD spoke to many of them about what it takes.

Janice Mac Avoy
Fried Frank (2021)

There was this famous line in the filing from a 2016 case about how you’re not an attorney who had an abortion; you’re an attorney because you had an abortion. That line wasn’t mine, but I think it spoke for so many of us who … I would not have become a lawyer if it hadn’t been for my access to abortion care. If I had been forced to have a child when I was 18 years old, I wouldn’t have gone to college. I wouldn’t have gone to law school. I would have had a shitty job and I would’ve been poor just like my parents. It enabled me to wait until I was financially and emotionally ready to be the kind of mom that my kids deserve to have.

Mary Ann Tighe
CBRE (2010)

What kind of student were you?
I was a great student. I was a good girl. I had no idea that there was more opportunity in being a bad girl.

You worked for Vice President Walter Mondale. How did that prepare you for real estate?
If you’ve worked in the White House or testified before Congress before turning 30, it’s hard to have people shake you up. What’s somebody going to ask you that’s scarier than having the Vice President of the United States ask you a question?

Do you ever get angry during negotiations?
I’ve mellowed with age, but remember, I’m Italian, and anyone will tell you that I’m a fairly intense personality. When I do get angry, it’s typically not a small thing. I think that there is a certain shock element in having it come out of the mouth of a seemingly nice woman.

Darcy Stacom
CBRE (2009)

Was it difficult that there were so few women in the field when you started?
Actually, it was a very positive challenge. I’ve always been a nonconformist. I’ve never owned a business suit and I never will. It’s just not me. A lot of brokers use entertaining as a means of creating new relationships and establishing new clients. I just didn’t do that.

I remember once being scheduled to play golf with [clients] and then they found out what my handicap was and they canceled. I realized that socializing wasn’t going to get me anywhere.

Alicia Glen
NYC deputy mayor (2015)

Do you ever get tired of being politically correct?
I may be accused of not saying the politically correct thing enough. I’m known as someone who pretty much speaks her mind and doesn’t try to play the game. If I say something that’s deemed politically correct, it’s because it’s correct.

You’re not welcome here

The industry isn’t just mostly male — it’s mostly white. Some of the minorities who’ve pushed through the prejudice shared their early experiences too.

Thad Wong
@properties (2023)

As a mixed-race kid with an Asian last name, did you deal with any racism?
In Chicago, when I moved here, I worked my way through college on the trading floor [at the Chicago Mercantile Exchange]. And that’s a very barbaric place. It’s almost like going back 50 years. What you saw and heard was prehistoric. I was called a chink a few times. They sounded so idiotic when they said it that it didn’t affect me negatively. Someone who says something so stupid … you almost have to laugh at them versus feel bad for yourself.

Meredith Marshall
BRP Companies (2022)

You were the first Black family on your block in East Flatbush. What was that like?
The first night, some people ripped off some of the siding from the house. There were some other “microaggressions,” as they call it today, but my parents were tough. They had a house — they dealt with it. Someone insulted me when I was young, and my father went at them with a tool. They had to hold him back.

Amar Lalvani
Standard International (2022)

What did your parents do?
My father was born and raised in New Delhi, and he moved to the U.S. in 1961. Of course, I heard the story a million times: He came with $21 in his pocket. The only place that would give him a full scholarship including stipend was in New Brunswick, Canada, so he moved there on his own.

When he went back to India to find a wife, he moved her from Bombay — where she was having a great time in art school — to Bartlesville, Oklahoma, to work for Phillips Petroleum. It was a company town; all the men wore the same suits, and we still have this paper — I think it was the Bartlesville Post — it said, “Indian man brings wife to Bartlesville.” My mom cried herself to sleep every night.

Ray McGuire
Banker and NYC mayoral candidate (2021)

You’re an outlier. Can you expect other people to succeed the way you did?
I shouldn’t be an outlier. I have spent a large part of my career making certain that even though I was a soul brother, I wasn’t the sole brother. Part of the pride that I take in 36 years in this business is to have extended the ladder, so that those others who had the skill set, who had the education, could have the opportunity to get into the room that I had.

You have said, “Once I take off my suit and put on a sweatsuit, I could easily be George Floyd.” Have you had any negative experiences with police?
Very few black people haven’t had an experience with the police. Three weeks ago, I get in a car, and we go two blocks. There’s a black driver, and there’s me. And there’s a police siren. Roll down the window, you’ve got two black guys in the car. “What are you guys doing?”

How do you handle that?
You’re a 6’4”, 200-pound Black man. Your hands go up. You respond when the questions get asked. You show no hostility. You show no movement of hands. You look directly in the eye, and no false moves. The result of which is we have no idea. The stories are out there. That’s our reality.

Having it all

From days broken down into 15-minute chunks to making your spouse your business partner, real estate players have employed creative strategies to keep living while living the business.

Jeff Blau
Related Companies (2012)

How do you balance work and young kids?
I see the kids in the morning. I usually don’t see them during the week at night, and then on the weekends, it’s all about the kids, 100 percent. It’s a trade-off.

Nancy Ruddy
CetraRuddy (2021)

What’s it like to work with your husband?
There’s a magic that happens, because John and I have very different worldviews but shared principles. Four times a year, I want to kill him, and I’m very open about it. Literally four times a year. But other than that, it’s really wonderful. We have a big studio with 80 people, and we’ve always shared an office. Three years ago, we moved after 28 years. I said to John, “This is your chance if you want to have a separate office.” We still decided we really wanted to be together.

Frederick Peters
Warburg Realty (2008)

Is your wife OK with that friendship? [with Fox Residential’s Barbara Fox]
As my wife likes to say, I have a career in which I take women alone into apartments. She had to make her peace with that long ago.

Dottie Herman
Douglas Elliman (2009)

How often do you and your husband see each other?
We don’t see each other much, especially not during the week. Any relationship takes compromises. I don’t think there’s a perfect formula for marriage. If it works for both of you, that’s what counts.

MaryAnne Gilmartin
Forest City Ratner (2010)

I read that your husband stays home with your kids.
I slay the dragon every day and my husband is the quiet warrior. He nurtures and cultivates our home life. It’s the secret to my success in so many ways.

Kevin Maloney
Property Markets Group (2014)

How did you meet your wife?
I was coming back from swimming at a community pool one morning and I saw a woman bent over a silver Porsche being frisked by two policemen. I was driving by and she looked really cute. I knew one of the cops so I stopped. He thought she was coming back from an all-night party and was drunk, but her position was that she was just a really bad driver. It turned out that she is really a bad driver.

Jeff Levine
Douglaston Development (2008)

How have you stayed married all these years?
Well, we were first too poor to divorce. Now we’re too opulent to divorce.

Insiders and outsiders

Real estate is a dynastic business, with empires passing down from father to son (or sometimes, daughter). But every so often, there’s someone that breaks the mold and comes out of nowhere. TRD has spoken to both the ultimate insiders, the dynasties and those who barraged their way in.

Jeffrey Gural
Newmark Knight Frank and GFP Real Estate (2012)

How did you get to be the chairman?
Nepotism. I had the intelligence to recognize it would be easier to go into a business that was family-owned than to try to be a hero. Not that I don’t totally respect people who didn’t have a leg up. I think that I proved myself to the employees by working hard. If you work hard, people will accept the fact that, “Yeah, okay, his father was one of the owners of the company, but he didn’t just go on vacation.”

Nathan Berman
Metro Loft Management (2017)

What do you remember about arriving in New York?
I was blown away. What impressed me most were jeans and dungarees. And I couldn’t believe the tube socks. How could they be so white, so clean? They didn’t have Tide in Russia.

Raphael De Niro
Douglas Elliman (2017)

You’ve appeared in some of your parents’ movies, right?
I did when I was a kid. I remember vaguely being on the set and having to repeat the scene over and over. It didn’t appeal to me. I still get residual checks from MGM for like $5.50 for “Raging Bull,” even though I was cut out of a short scene.

Ofer Yardeni
Stonehenge Management (2013)

How did you get into real estate?
Completely by default. I was single in New York and every woman that I met, her parents were in real estate. Very early, I realized real estate in New York is like celebrity in L.A. We are consumed by it. People wake up in the morning and talk about real estate. When they have sex, they talk about real estate. Even if you have only a cheap apartment, you talk about real estate.

Anthony Scaramucci
Skybridge Capital (2019)

I have noticed you make a point of saying that you went to Harvard. Why is that?
Arriviste. You have to understand something: You’re being profiled. I’m being profiled. So when somebody on late-night television is trying to equate me to the Jersey Shore because I’m Italian, or to the Mafia, I say, “Guys, time out a second. I went to Harvard Law School, okay?”

Douglas Durst
Durst Organization (2007)

What’s the upside of working in a family business?
That you’re working with people that have the same or similar thought processes and that you can rely on.

What’s the downside of working in a family business?
There’s emotional and other relationship baggage that comes with working in a family business.

Robert Lapidus
L&L Holding (2013)

What was it like being a cabana boy?
I got paid a salary of $87 a week, but I got $600 a week in tips because I hustled. Hustle pays off. It helped me pay for my wife’s engagement ring.

Robert Gladstone
Madison Equities (2016)

During your time working construction at your family’s projects, you lost parts of your fingertips in an accident.
I was electrocuted with 220 volts. After I was all stitched up … and as I got into a cab, Paul Simon’s “Duncan” was playing, and the last verse was, “I was playing my guitar, lying underneath the stars, just thanking the Lord, for my fingers.” That’s a God moment.

Hard-won advice

Success in real estate is easier said than done, but here are some of the rawer and more honest pieces of advice titans have dished out over the years in these pages.

Howard Lorber
Vector Group (2006)

Give advice to someone 20 years younger.
It’s easy, if you work like a dog.

Stephen Siegel
CBRE (2006)

What is the best piece of advice you ever received?
Always treat people honestly. There’s no such thing as a white lie. There’s only a lie.

David Lichtenstein
Lightstone Group (2016)

What’s your advice for someone 20 years younger?
Don’t become a square watermelon. Try to remember who you were when you were a child and your soul was given to you — before it was squashed by the haters and the cynics.

Alicia Glen
NYC deputy mayor (2015)

What’s the best advice you’ve received?
Life is long. Most people think life is short, so they have a vision of what they want to be when they grow up and then they’re like gerbils in a wheel. At Goldman, they used to joke, “You’re the only person who’s been a tenant organizer and this and that, who’s a managing director running a $3 billion business, who’s a well-known lefty.” I worry that kids today are so focused on becoming a partner at a law firm, [they’ll] miss all the twists and turns that create amazing opportunities.

Nathan Berman
Metro Loft Management (2017)

A few years ago, Crain’s dubbed you the King of FiDi. What did you think about that?
I don’t know how the writer came up with that. If I could have stopped him, I would have. Ego is the most expensive thing that most people can’t afford.

Philosophy

Who needs the stoics when you’ve got real estate moguls?

Michael Shvo
Shvo (2014)

How do you feel about being known as the “bad boy” of real estate?
I can’t tell you why people think one thing or the other about me. When you change the status quo, there are people that like it and people that don’t like it. I would hope I have critics. If everyone thinks it’s OK, then there’s truly no value to the creation.

Henry Elghanayan
Rockrose Development (2013)

Do you need to have a certain amount of ego to be a successful developer in New York City?
You must not only have an ego, you must have a super-optimistic view of life. I have an unnaturally optimistic view on life — it’s a sickness. If you understood the real dangers involved in doing a project, you would never do one.

Pam Liebman
Corcoran Group (2007)

What’s something people don’t know about you?
I like rap music. My iPod is full of rap music with everyone from Ludacris to Jay-Z to the Game. When people borrow my iPod, they’re like, “What is this?”

Barbara Corcoran
Corcoran Group (2006)

How do you size up people when you first meet them?
I have two categories and two subcategories for everyone. First, if they are good or bad; then, if they are an expander or a container. Expanders want to push out and create bigger things. Containers want to control, and they are both good. One is not less important than the other.

Jeff Greene
Investor (2013)

You’re known as a very tough boss, and you’ve been nicknamed “Mean Jeff Greene.”
I don’t think I’m mean. I put a lot of pressure on myself to do well, and I put the same pressure on the people around me. For the most part, people who have worked for me tell me they didn’t like me much, but they learned a lot. I’m very proud of that. It would be worse if they said, ‘Boy, he was a sweet guy, but I learned nothing.’

Robert A.M. Stern
RAMSA

How do you feel about the term “starchitect?”
That architects have been given some kind of star status is nice. On the other hand, I don’t think architects should be celebrated like movie stars. We’re much more interesting than movie stars and much more important, and what we do is much more enduring. If you don’t like the movie you’re watching, you can turn it off or walk out of the theater or fall asleep. I do all of those things. But if it’s a building and it’s across the street from your window and it’s an abomination, what are you going to do about it? Not much.

Pain and redemption

Personal battles, family tragedies and how to bounce back.

Charles Kushner
Kushner Companies (2007)

Have you had any resolution with your sister and her husband?
I mean, it’s a family tragedy what happened. I believe that God and my parents in heaven forgive me for what I did, which was wrong. I don’t believe God and my parents will ever forgive my brother and sister for instigating a criminal investigation and being cheerleaders for the government and putting their brother in jail because of jealousy, hatred and spite. On my worst day in prison, I wouldn’t trade places with my brother and sister, and yet I know what I did was wrong.

Dan Doctoroff
Former NYC deputy mayor and Bloomberg CEO (2015)

What’s been your toughest personal obstacle?
The most difficult thing I’ve had to deal with is the death of my parents. They both died young and from rare diseases.

Do you worry about dying young because of that?
My dad and my uncle died of ALS, Lou Gehrig’s disease, so there’s clearly a genetic component. That creates a bit of a specter that comes and goes. [However] it’s not like I say, ‘I’ve got to get everything done now because I’m afraid I’m going to die tomorrow.’

[In 2021, Doctoroff announced that he, too, was diagnosed with ALS, and stepped back from his companies.]

Barry Sternlicht
Starwood Capital (2020)

Your father was a Holocaust survivor. Did he ever discuss that with you?
Yes, but not until I was 38. I took him back to Poland. I think that was when he first told me that he killed someone during the war. He was not in a camp. He was lucky to survive in the mountains, and he was liberated by the Russians.

How do you think that experience shaped his worldview and how he raised you?
I think he had a hard time trusting people. He always felt a little bit like an outsider, even though he married a gal from Brooklyn. He obviously taught me to be tough. My worst day was probably better than his best day during that eight- or nine-year period.

Ian Bruce Eichner
Continuum Company (2011)

You defaulted on CitySpire on 56th Street and the Bertelsmann Building at 1540 Broadway, both in the early 1990s, and at the Cosmopolitan in Vegas in 2007. Are you feeling discouraged today?
No. Like I try to explain to my kids, there’s only one thing you’re in control of: your level of effort. I’m not a genius when I make $50 million. I’m not a failure if I lose it.

Richard Meier
Richard Meier & Partners (2010)

Is there anything you regret, any mistakes you’ve made in your career?
If so, I’ve blocked it out.

[In 2018, Meier was forced out of his firm after multiple allegations of sexual harassment.]

Danny Meyer
Union Square Hospitality (2012)

Does your company own any of the buildings where your restaurants are situated?
We own the space that is Gramercy Tavern.

Is that the only one?
Sadly. I’m sometimes frustrated we haven’t shared in the real estate boom that some of our restaurants have helped make happen.

Todd Michael Glaser
Developer (2022)

What’s your biggest regret?
I don’t think I have one. I’ve done everything I’ve wanted to do. I’m a simple guy. I’m not very social, I’m not very big on people. I don’t want to hear, “Jack and Jill went up the hill to fetch a pail of water. Jack fell down and broke his crown.” … I just want to know Jack’s dead.

Eliot Spitzer
Spitzer Enterprises (2019)

What have you learned about second chances and redemption in the years since you resigned as governor?
People are, by and large, forgiving. There are people who are affirmative, who understand there are flaws and failures, and opportunities to come back. That is one of the wonderful things about human nature.

Ian Schrager
Hotelier (2012)

In 1979, you and your business partner Steve Rubell pleaded guilty to income tax evasion at Studio 54 and served nearly two years in prison. What did you take away from that?
It was unreported $400,000 in gross income. I guess I must’ve been thinking the rules didn’t apply to me. It didn’t take away my enthusiasm or passion for life, but I came out of it knowing that I had to play by the rules that everyone else does. … We lost everything. We had nothing. [But] we were able to come back and pick ourselves up off the floor and dust ourselves off.

Howard Lutnick
Cantor Fitzgerald (2015)

What is it like to be the face of Sept. 11?
If I go out to dinner, someone will come up to me and say they know a widow or a family. It’s really incredible. To those who have had loss, memory is the most beautiful of your senses. So memory and time takes out the pain.

Do you have regrets?
Sure. I wish we were never in the World Trade Center. I wish my brother never came to work for me. I wish I never hired all my friends.

— Interviews by: Rich Bockmann, Kathryn Brenzel, Katherine Clarke, Lauren Elkies, Erik Engquist, Erin Hudson, David Jeans, Leigh Kamping-Carder, Amir Korangy, Will Parker, Konrad Putzier, Hiten Samtani, Sarabeth Sanders, E.B. Solomont and Candace Taylor